Poverty and income inequality undermine women’s health in a myriad of ways. This article discusses findings from the Full Plate Project, which addressed women’s experience of food security, obesity, and chronic disease in Atlantic Canada. Through first-hand accounts, it identifies a vicious cycle surrounding the food insecurity–obesity paradox. The cycle’s core elements included experiences of poverty, food insecurity and nutritional deprivation, weight gain leading to obesity, stress, and experiences of chronic illness. These mainly qualitative findings provide a vivid and multi-layered analysis of the effects of inequalities on health. A majority of Full Plate participants were lone mothers and unattached women, and existing outside of a two-adult member household framework. The vicious cycles experienced are intertwined and cannot be addressed by compartmentalising elements of health or social services. Evidence indicates that policies must respond fully to the social determinants of health and multiple inequalities related to poverty, gender, age, mobility, disability, location, culture, coping skills, and other dynamics.